Chlorination of alkenes with Cl2 to give vicinal dichlorides
Description: Treatment of alkenes with chlorine (Cl2) in an inert solvent like CCl4, alkanes, or CH2Cl2 leads to formation of vicinal dichlorides (1,2-dichlorides)
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Chlorine has an equal chance of attacking only if the site is not sterically hindered right. Or else the less sterically hindered site would be preferred?
Backside attack will occur even if the position is tertiary. The reason is that the C-Cl bond length on the tertiary position is *much* weaker (and has much longer C-Cl bonds) so it’s not like a traditional SN2 type reaction.
James, great study source. I wish you would include correct equilibrium/forward reaction arrows!
Would the reaction be the same with Br2?
Yes, essentially it will be.
what solvent should we use to get maximum yield?
Use a non polar solvent like dichloromethane or an alkane.